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Angew Chem Int Ed Engl. 2014 Apr 25;53(18):4690-3. doi: 10.1002/anie.201400420. Epub 2014 Mar 25.

A convenient photocatalytic fluorination of unactivated C-H bonds.

Author information

  • 1Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada).

Abstract

Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives.

KEYWORDS:

CH activation; amino acids; photochemistry; polyoxometalates; tungsten

PMID:
24668727
DOI:
10.1002/anie.201400420
[PubMed - indexed for MEDLINE]
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